Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 38, Pages 12299-12302Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804848
Keywords
alkaloids; cascade reactions; heterocycles; photochemistry; total synthesis
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Funding
- National Natural Science Foundation of China [21732005]
- National Science and Technology Major Projects for Major New Drugs Innovation and Development [2018ZX09711003-015, 2017ZX09101003-005-004]
- 111 Project [B18035]
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The development of efficient syntheses of complex natural products has long been a major challenge in synthetic chemistry. Designing cascade reactions and employing bioinspired transformations are an important and reliable means of achieving this goal. Presented here is a combination of these two strategies, which allow efficient asymmetric synthesis of the cinchona alkaloid (+)-cinchonidine. The key steps of this synthesis are a controllable, visible-light-induced photoredox radical cascade reaction to efficiently access the tetracyclic monoterpenoid indole alkaloid core, as well as a practical biomimetic cascade rearrangement for the indole to quinoline transformation. The use of stereoselective chemical transformations in this work makes it an efficient synthesis of (+)-cinchonidine.
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